Advantage of in situ generation of N-arylsulfonyl imines from α-amide sulfones in the phase-transfer-catalyzed asymmetric Strecker reaction

被引：55

作者：

Ooi, Takashi ^{[1
]}

Uematsu, Yukitaka ^{[1
]}

Fujimoto, Jun ^{[1
]}

Fukumoto, Kazuhiro ^{[1
]}

Maruoka, Keiji ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, Dept Appl Chem, Chikusa Ku, Nagoya, Aichi 4648603, Japan

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 08期

关键词：

alpha-amido sulfones; alpha-amino nitriles; chiral quaternary ammonium iodide; potassium cyanide; Strecker synthesis;

D O I：

10.1016/j.tetlet.2006.12.122

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly efficient, catalytic enantioselective synthesis of N-arylsulfonyl alpha-amino nitriles from the corresponding alpha-amido sulfones has been achieved under toluene-aqueous potassium cyanide biphasic conditions using chiral quaternary ammonium iodide (R,R,R)-1 as an effective phase-transfer catalyst. This Strecker synthesis involving the in situ generation of the reactive N-sulfonyl imines is advantageous for the cyanation of the substrates having primary and secondary alkyl substituents. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：1337 / 1340

页数：4

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